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Molecules 2011, 16(11), 9451-9466; doi:10.3390/molecules16119451
Article

Anti-Inflammatory and Free Radial Scavenging Activities of the Constituents Isolated from Machilus zuihoensis

1,2
, 3
, 1,2
, 4
, 5,6,*  and 2,7,*
1 School of Pharmacy, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan 2 Graduate Institute of Pharmacognosy, College of Pharmacy, Taipei Medical University, Taipei 110, Taiwan 3 Biomedical Technology and Device Research Laboratories, Industrial Technology Research Institute, Hsinchu 300, Taiwan 4 Graduate Institute of Pharmaceutical Sciences, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan 5 Institute of Biological Chemistry, Academia Sinica, Taipei 115, Taiwan 6 Institute of Biochemical Sciences, College of Life Science, National Taiwan University, Taipei 106, Taiwan 7 Center for Reproductive Medicine & Sciences, Taipei Medical University Hospital, Taipei 110, Taiwan
* Authors to whom correspondence should be addressed.
Received: 19 September 2011 / Revised: 1 November 2011 / Accepted: 2 November 2011 / Published: 10 November 2011
(This article belongs to the Section Metabolites)
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Abstract

A new biflavonol glycoside, quercetin-3-O-β-D-glucopyranoside-(3¢→O-3¢¢¢)- quercetin-3-O-β-D-galactopyranoside (9), together with eight known compounds was isolated for the first time from the leaves of Machilus zuihoensis Hayata (Lauraceae). The structure of compound 9 was elucidated by various types of spectroscopic data analysis. Analysis of the biological activity assay found that compound 9 showed significant superoxide anion scavenging activity (IC50 is 30.4 μM) and markedly suppressed LPS-induced high mobility group box 1 (HMGB-1) protein secretion in RAW264.7 cells. In addition, the HMGB-1 protein secretion was also inhibited by quercitrin (3), ethyl caffeate (6), and ethyl 3-O-caffeoylquinate (7) treatment. In the LPS-stimulated inducible nitric oxide synthase (iNOS) activation analysis, two known compounds, quercetin (1) and ethyl caffeate (6), were found to markedly suppress nitric oxide (NO) production (IC50 value, 27.6 and 42.9 μM, respectively) in RAW264.7 cells. Additionally, it was determined that ethyl caffeate (6) down-regulated mRNA expressions of iNOS, IL-1β, and IL-10 in the LPS-treatment of RAW264.7 cells via a suppressed NF-kB pathway. These results suggested for the first time that the new compound 9 and other constituents isolated from M. zuihoensis have potential anti-inflammatory and superoxide anion scavenging effects. These constituents may be useful for treating various inflammatory diseases.
Keywords: Machilus zuihoensis; anti-inflammatory; quercetin-3-O-β-D-glucopyranoside-(3¢→O-3¢¢¢)-quercetin-3-O-β-D-galactopyranoside; ethyl caffeate; quercetin Machilus zuihoensis; anti-inflammatory; quercetin-3-O-β-D-glucopyranoside-(3¢→O-3¢¢¢)-quercetin-3-O-β-D-galactopyranoside; ethyl caffeate; quercetin
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Mao, Y.-W.; Tseng, H.-W.; Liang, W.-L.; Chen, I.-S.; Chen, S.-T.; Lee, M.-H. Anti-Inflammatory and Free Radial Scavenging Activities of the Constituents Isolated from Machilus zuihoensis. Molecules 2011, 16, 9451-9466.

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